2-Amino-3-(4-aminophenyl)propanoic acid

Details

• Internal ID: c154209b-aa7c-4cbe-81ca-33761e3931b2
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Phenylalanine and derivatives
• IUPAC Name: 2-amino-3-(4-aminophenyl)propanoic acid
• SMILES (Canonical): C1=CC(=CC=C1CC(C(=O)O)N)N
• SMILES (Isomeric): C1=CC(=CC=C1CC(C(=O)O)N)N
• InChI: InChI=1S/C9H12N2O2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,10-11H2,(H,12,13)
• InChI Key: CMUHFUGDYMFHEI-UHFFFAOYSA-N
• Popularity: 87 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₂N₂O₂
• Molecular Weight: 180.20 g/mol
• Exact Mass: 180.089877630 g/mol
• Topological Polar Surface Area (TPSA): 89.30 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): 0.22
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 2-amino-3-(4-aminophenyl)propanoic acid
• 4-Amino-dl-phenylalanine
• p-Amino-dl-phenylalanine
• 4-Aminophenylalanine
• H-DL-Phe(4-NH2)-OH
• Phenylalanine, 4-amino-
• p-AMINOPHENYL ALANINE
• H-P-AMINO-DL-PHE-OH HYDRATE
• para-Aminophenylalanine
• L-2-Amino-3-(4-aminophenyl)propanoic acid
• D-4-aminophe
• L-4-aminophe
• 4-Aminophenylalanine #
• H-p-Amino-Phe-OH HCl
• p-Amino-D-phenylalanine acid
• MFCD00069926
• MFCD00069927
• p-Amino-DL-phenylalanine hydrate
• EINECS 220-869-1
• D-Phenylalanine,4-amino-
• beta-(p-Aminophenyl)alanine
• DL-Phenylalanine, 4-amino-
• SCHEMBL43851
• 4-Amino-D-phenylalanine Acid
• H-D-Phe(4-NH2)-OH
• BDBM36558
• CHEBI:143078
• DTXSID201313036
• BCP11627
• BCP34212
• NSC21918
• NSC29446
• MFCD00007917
• NSC 21918
• NSC 29446
• NSC-21918
• NSC-29446
• AKOS005174947
• AM82698
• FS-4735
• PD158335
• SY065205
• SY122108
• CS-0204431
• FT-0633172
• FT-0634556
• FT-0643864
• FT-0657837
• N12064
• A800554
• 4-Amino-DL-phenylalanine (H-DL-Phe(4-NH2)-OH)
• 4-Amino-Phe;L-4-NH2-Phe-OH;H-Phe(4-NH2)-OH
• J-017442
• 2-Amino-3-(4-aminophenyl)propanoic acid DL-Phe(4-NH2)-OH

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9825	98.25%
Caco-2	+	0.8164	81.64%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Lysosomes	0.4089	40.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9772	97.72%
OATP1B3 inhibitior	+	0.9517	95.17%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8866	88.66%
P-glycoprotein inhibitior	-	0.9903	99.03%
P-glycoprotein substrate	-	0.9470	94.70%
CYP3A4 substrate	-	0.8230	82.30%
CYP2C9 substrate	-	0.6061	60.61%
CYP2D6 substrate	-	0.7476	74.76%
CYP3A4 inhibition	-	0.8294	82.94%
CYP2C9 inhibition	-	0.9586	95.86%
CYP2C19 inhibition	-	0.9774	97.74%
CYP2D6 inhibition	-	0.9713	97.13%
CYP1A2 inhibition	-	0.9009	90.09%
CYP2C8 inhibition	-	0.9750	97.50%
CYP inhibitory promiscuity	-	0.9821	98.21%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5611	56.11%
Carcinogenicity (trinary)	Non-required	0.7657	76.57%
Eye corrosion	-	0.9965	99.65%
Eye irritation	-	0.6117	61.17%
Skin irritation	-	0.7331	73.31%
Skin corrosion	-	0.8928	89.28%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8293	82.93%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.5332	53.32%
skin sensitisation	-	0.8249	82.49%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8536	85.36%
Acute Oral Toxicity (c)	III	0.5544	55.44%
Estrogen receptor binding	-	0.9250	92.50%
Androgen receptor binding	+	0.5478	54.78%
Thyroid receptor binding	-	0.8674	86.74%
Glucocorticoid receptor binding	-	0.7940	79.40%
Aromatase binding	-	0.8046	80.46%
PPAR gamma	-	0.5982	59.82%
Honey bee toxicity	-	0.9707	97.07%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	-	0.5080	50.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.89%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.00%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	92.52%	83.82%
CHEMBL3492	P49721	Proteasome Macropain subunit	90.80%	90.24%
CHEMBL221	P23219	Cyclooxygenase-1	90.15%	90.17%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	89.84%	92.29%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.17%	95.50%
CHEMBL1255126	O15151	Protein Mdm4	88.65%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.51%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.65%	91.11%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.39%	97.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.01%	94.45%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	85.04%	95.48%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.84%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.78%	96.95%

Plants that contains it

• Vigna vexillata

Cross-Links

• PubChem: 95174
• LOTUS: LTS0064603
• wikiData: Q104965167